strap-on sex

I had lost the bet and now Jenny was going to collect. She had a really naughty smirk on her face as she let me in.

“I was beginning to wonder if you were coming over.”

“I don’t welch on a bet, even though I don’t know what you’re up to.”

“Just a bit of revenge, you might get to like it too.”

“So, what do you want me to do?”

“Strip, then I can prepare you.”

“Prepare…?”

“Just do it Steve.” Shrugging, I took off all my clothes. “Boxers too.” With a sigh I complied, revealing a cock that was already hard. “My, my, looking forward to this are we?”

“I don’t know yet do I?”

“The first thing we have to do is remove all your body hair.”

“All?”

“Except your head, we just need to cut that short.”

It took her over an hour. An hour that was quite painful at times. She didn’t just use a razor, but waxing strips too, mainly on my balls and legs. In the end she was satisfied that the only hair left on my body was on my head. She went into the bedroom and came back with some clothes.

“Put these on.”

I looked at them.

“This is a maids uniform.”

“I know, put it on.”

A little unsure I began to put the clothes on. Bra first. Jenny gave me two gel falsies to pad me out a bit. Next was the dress. It was very short, barely covering my ass. She handed me the black stockings, hold-ups they were. As I slid them up my now smooth legs they felt really good. I pulled up the silky white knickers next. Another good feeling as the shiny material cupped my shorn balls. Finally came the shoes, black, with a three inch squared heel. Jenny bade me stand. The heels made my legs look quite feminine. Next she handed me the lacy wristlets and apron. The final touch was a blonde wig with maid cap on top. Jenny looked me up and down.

“You look good as a woman. I’ll get some make-up to complete the job.” After she disappeared into the bedroom again I caught a glimpse of myself in a mirror. Shockingly she was right, I did look good. Jenny came back and began putting the make-up on. Lipstick, blusher, eye-liner, eye shadow, the works. I looked in the mirror again and didn’t recognise myself. I did however quite fancy the woman I had become. “Very cute.” Jenny said. “But you need a new name. Not Stephanie, too obvious.” She snapped her fingers. “Got it! You can be Emma.”

“Okay, I’m Emma. Now what? I don’t suppose you went to all this trouble just to make me hot for myself.”

“Hot for yourself huh? Maybe you’ll be more into this than I hoped.” She smiled. “I’m going to train you to be spit-roasted like a woman.”

I gulped.

“You mean…”

“Yes. Follow me Emma.” She led me into the bedroom.

“If I agree to this, will you do something for me?”

Jenny paused.

“Maybe. I like a challenge. What exactly are you proposing?”

“If I go through with this, which I admit is turning me on; I want to see you…”

“What!? Spit it out Emma.”

“I’d like to watch you fucked in the ass too.” I blurted out.

Jenny smiled thoughtfully.

“Okay, you’re on. Now get in here and kneel down.” Stunned by her acceptance I did as I was bid. “First of all, I’ll need to widen your asshole, so put this in.” She handed me a tapered butt-plug with a harness attached. I eased my panties down and attempted to push the plug in. “Not like that. Let me.” Jenny took the plug from me and applied some lube. She bent me forward and slid it in. “Do the straps up, it will hold it in for you.” Again I complied. It was a strange feeling, but not entirely unpleasant. “The next thing is to teach you to suck cock.” I looked up hopefully. “No, I’m not sucking you off; I’m going to use this on your mouth.” She took out a strap-on and stepped into it. I was still kneeling in front of her and the plastic prick was inches from my face. “Lick it. Lick it like you would like to be licked.” Tentatively I stuck my tongue out and ran it around the head of the dildo. “Good. Now take it into your mouth.” I opened my mouth and took the strap-on between my lips. I had about half of it in when I began to gag and started to pull back. Jenny grabbed the back of my head and pulled me forward, sinking the dildo to the hilt. After the initial shock I found myself not disliking the feeling. “You will make a great cock-sucking slut. Are you ready to try the real thing?” Now lost in sexual desire, I nodded yes. “Good.” She pulled out of my mouth. “Follow me then.” I pulled up my panties and followed her to the door where she handed me a coat.

————————————–

I don’t know where Jenny took me, it was a seedy looking place from the outside, completely non-descript. Inside though, it was obviously some sort of sex club.

“See anyone you fancy to take your anal cherry?” I shook my head, nervous again now. “I’ll pick then. You get on all fours on that bed.” She pointed to a bed on a stage. I looked at her. “If you back out now, you’ll never get to see me with a doggie will you?” Dumbly I nodded and took up my position. She came over with two guys who placed themselves one in front and one behind. The guy behind flicked up my skirt and pulled down my knickers. The butt-plug was still in place. He unstrapped it and pulled it out. I moaned slightly and then felt his hands on my ass cheeks, easing them apart. His knob was suddenly touching my asshole. “Relax.” I heard Jenny say. With a sudden thrust I had a dick up my butt. I opened my mouth in surprise and that was filled by a cock too. The warm pulsing feeling from both pricks was strangely good. They both sank deep into me. I had pubic hair in my face and could feel balls on my ass cheeks. “Well done Emma. They’re both all the way in. Now go for it.” I began to rock backwards and forwards as the two guys took it in turn to thrust into me. My own cock felt as if it had grown huge. I wanted to touch it, to relieve the pressure, but instead I felt a moist mouth enveloping it, Jenny’s mouth. The guy in my ass came at the same time as I did, my cum going into Jenny’s mouth, his spraying into my back passage. Moments later the guy in my mouth began to twitch and then he shot his load into my throat. The hot sticky liquid tasted like nothing I’d ever tasted before. I suddenly knew that I wanted more.

“Jenny, get some more. I want more.”

“I thought you wanted to see me fucked in the ass?”

“I do, but now I want more cock. Please?”

She sighed and nodded. At once I was surrounded by cocks. I was rolled over onto my side and my legs were pushed up towards my chest. A dick entered my ass again, easier this time, and another was pushed into my mouth. One was placed in either hand too. Those I began to jerk off. Then I felt another cock between my thighs. The knob end thrust through and brushed my own again raging hard-on. I was in a sexual haze like never before and just let them pummel my body while still wanking off the two in my hands. The prick up my butt spurted off and was replaced by another. The one in my mouth followed, the hot spunk coating my throat and then covering my face. I jerked off the two in my hands, their come splashing my face as well. The last anal intruder came at the same time as the one using my closely pressed together thighs. As their come spurted out, covering my ass and my cock, my dick exploded unassisted, splashing onto my stomach.

Jenny knelt beside me, licking some of the come from my face.

“Happy now?” She asked raising her eyebrows.

“Thank you for showing me something so new.” I gasped. “I never knew that being fucked was like this.”

“My turn now then. Move over so I can get ready.”

“You don’t have to do anything Jenny, this feeling is enough compensation.”

“I said I would, so I will. Sit up and watch.” I pushed myself up on my elbows, oblivious to the come drying on my face, ass and stomach. Jenny was on all fours next to me. A huge guy appeared behind her, a monstrous erection jutting out from between his legs. She gasped as he mounted her, sinking his swollen member into her welcoming ass. “Oh!” She gasped. “That’s filling me up so much.” I watched transfixed as the huge dick thrust in and out of the slim blonde. “Steve! Emma I mean, slide over here, I want your cock too.” Obligingly I did so. She took my burgeoning erection into her soft mouth once more. “I can taste two lots of come on it.” She muttered. I looked up at the guy still stoically pounding her from behind. “Oh god, his knob is all the way in me. I’m so full.” She grunted. “He’s coming, he’s coming!” She shouted out, leaving my dick waving in the air. “He’s filling me up with come.” With that she passed out, leaving me frustrated and with a raging stiffy.

————————————–

“Let me take care of that.” A vaguely familiar redhead said, dropping her mouth to my cock. She was good and I came quickly. She swallowed the whole load, not spilling a drop. “Nice. Are you busy at the moment?” I shook my head. “Want to come with me for a while?” I nodded. “Come on then.”

The redhead, who I now recognised as Karen, the girl from my local shop, led me into a side room. She closed the door behind me.

“I thought you might be a repressed bi-sexual, but I didn’t think you were a cross dressing masochist.”

“I…I’m not. I think.”

“Looks like it to me.” She smirked. “Kneel.” I dropped to my knees. “Good. Now lie on your back.” I obeyed again, smoothing down my skirt over my stiffening cock.

“Leave it out. In fact pull your dress up, let me see your shameful dick.” I complied. “Lie still.” She picked up a big candle and lit it. I watched her apprehensively as she stood over me, the lit candle in her hand. She tilted it and dropped melting wax on my cock. I winced and my dick twitched. “Thought so.” She put the candle down and slipped off her knickers. Picking the candle up again she knelt over my face. “Lick.” I stuck out my tongue apprehensively and lapped at the folds of her pussy as she dropped more wax onto my dick and shaved balls. “That’s good. Keep going.” She panted. I plunged my tongue into her slit, causing a slight gasp. Still she dribbled wax onto my groin. Despite the pinpricks of pain my cock was getting hard, and not just with the wax solidifying around it. Karen shifted my position. She pulled my legs up either side of her so I was balancing on my shoulders, my tongue still exploring her pussy, my waxed dick and cum-seeping ass in front of her face. She pushed the unlit end of the candle into my butt. It slid in easily. For a while I felt nothing and then the wax made its way down the candle and onto my ass-hole. The pain was only momentary but intense. It also felt good. Karen stood reluctantly, taking her sweet tasting cunt away from my questing tongue. “Stay there. I need to get some things.”

I waited in my strange posture, candle wax running into my ass-crack, wondering why I felt the need to be dominated. I heard Karen return.

“Good girl.”

“I’m not…”

“But you want to be. Sorry, but I can’t help you there.” With that she cuffed my hands beneath me and then secured them to the floor. She did the same with each ankle, pinning me into this awkward contortion, my waxed cock pointing at my own face. “Now I’m going to stuff this into that slutty ass.” She said, holding a long double-ended dildo in front of my face.

“No! It’ll never fit!!”

“Don’t be so negative, of course it will.” With that she pulled the candle from my butt and thrust almost half of the dildo in instead. I moaned in pleasure, what a sensation! My cock was expanded so much that the wax was starting to crack and fall away into my face. Karen leant down and swept it away before easing the monster dildo part of the way out of my ass and then thrusting down again. Now I was impaled on almost half of it. She smiled, raised her skirt and stood over me. She rested the other end of the dildo at the entrance to her snatch and slowly sank herself onto it. She began to ride it, slowly at first and then building up speed. The faster she went, the farther the dildo was pushed into my butt. “Soon, soon.” She panted. “Coming soon.”

“Oh, but you will come. You’ll come by yourself slut.” She panted just before a juddering orgasm shook her. Weakly she raised herself from her end of the dildo.

“Make me come.” I begged again. Karen quickly recovered and she put her hands around the phallus, still glistening with the juice from her pussy. Her eyes shone as she began to work the fake cock further and further into my ass. All at once my dick began to twitch and my spunk shot into my face. I opened my mouth to receive it.

“Such a slut. Coming just from having your ass fucked. And then swallowing your own spunk.” Karen laughed. “Well, time I was going.” She got up and began to walk away.

“You can’t leave me like this.” I called out.

“Of course I can. It’s someone else’s turn to play now.”

————————————————————–

I was left for twenty minutes in that contorted position, my dick dripping cum onto my face and the huge dildo stuck in my ass. And then I heard someone enter the room. I hoped it was Jenny come to take me away, but I was disappointed. There was a click of heels as the newcomer walked around me out of my vision.

“I’m glad Jenny was wrong about you.”

“Who ..?”

“I’m your new mistress.” She came into view. It was Sharon! “I won you in a bet with Jenny. She didn’t think you’d cum from having your ass fucked by a dildo, but she was wrong and now you’re mine.” She ran her hand over my stockinged leg.

“What… what are you going to do?”

“Well first, I’m going to have two cocks stuck into your butt. At the same time!”

“NO! I’m not big enough down there.”

“But you are now; your nearly virgin ass has stretched out already.” She clicked her fingers. At once there were two men stood over me. I could see their naked dicks quivering above me. They stood back to back, astride a leg each, pointing their dicks at my still filled asshole. Sharon reached forward and eased the monster phallus from me. Before the hole could shrink both cocks plunged in. My ass was suddenly full of throbbing hot meat. My own dick began to stiffen again, I couldn’t believe it. What sort of slut was I? The two intruders began to move. One pulled part way out and then thrust back in; the second one did the same. They took it in turns pistoning in and out of my butt, gradually increasing in speed until it felt like they were both permanently deep inside me. Sharon crouched over my face still caressing both my stocking-clad legs. She leant forward between the two legs of those above me, still pile-driving me, and licked at the pre-cum now oozing from my raging hard-on. I could feel my orgasm building. Before I came both dicks in my ass suddenly shot their load, filling me with more cum than ever. They both stayed in me until they had stopped coming, before withdrawing and vanishing. Sharon held my engorged dick, preventing me from letting loose. “MMmm. There’s so much cum in you it’s seeping out.” She laughed. She was right, I could feel spunk running between my buttocks and down towards my balls. Still holding onto my dick she lent forward again and began to lap up the escaping jizz. “Tasty.” She cooed. My dick felt like it was going to explode now, so much so that I was whimpering. Finally Sharon relented. She dropped her mouth around my aching cock and released her grip. Mere seconds after her tongue had begun to tease me I shot my wad into her throat. She pulled away and the rest of my load went into my face again. Sharon seemed amused by this. “I wonder what you’d look like covered in cum?” She mused. “Still, that can wait. I have to get you ready for your next game.” I wasn’t sure I liked the sound of that.

Sharon untied me and helped me to my feet, waiting until I got the feeling back into my limbs before leading me to a bathroom.

I did as I was bid, giving myself an enema and washing the cum and sweat from my body. Then, freshly laundered, I stood before my new mistress. Sharon looked me up and down. “Not much to work with, although the legs look good.” She smiled to herself. “You’ll make a fine toy for me to dress up and play with.” I wasn’t sure I liked the sound of that. I knew Jenny would never go too far, but Sharon? Sharon had a mean streak. “Put those on.” She commanded, handing me what looked like a pair of black latex panties. Except they weren’t panties. In the back was something like a large dildo. In the front was a pocket that was obviously where my cock was to go. Obviously because in front of that was a fake cunt. Any cock entering that would be rubbing against my own dick, held in the pocket. Gingerly I pulled the strange garment up my legs. “Your cock first.” Sharon said helpfully. I slipped my dick into its latex prison. This left the dildo poking against my butt hole. “That too.” Sharon was grinning evilly at my discomfort.

“Can I have some lube please?” Sharon raised an eyebrow. “Mistress?” I hazarded.

She nodded.

“Better.” She squeezed some lube into her hand and then worked it around the dildo head, sticking a finger into my ass to lube that too. She positioned the thing at the entrance and pushed. It went deep into me. Despite my predicament I couldn’t help but enjoy the feeling of something in my ass again. Sharon crouched behind me as I smoothed the latex briefs down. Suddenly the thing in my butt wasn’t solid anymore. I looked around puzzled. “The sheath in you can expand to take anything up to ten inches long. Won’t that be nice?” I gulped at the thought. “Now here’s the rest of your outfit.” She said pointing to a pile of clothing. “You have half an hour to get it on, then I’ll be back to finish up.” Sharon left.

I looked at the neatly folded pile. It was some kind of latex nurses uniform. The first thing was a pre-filled bra. I pulled it on. It gave me a bosom somewhere in the region of 36D. The rest of the uniform was donned quickly. The latex stockings were a bit tricky to get on smoothly and when I put on the six-inch heeled shoes I wondered how I was going to be able to walk. I left off the hat because I had an idea that Sharon was going to bring me another wig. As I was ready before her return I decided to practice walking in the tall heels. It wasn’t as hard as I’d thought. I was feeling unaccountably pleased with the way I moved when Sharon came back wearing a similar outfit to the one I now wore. She looked at me appraisingly.

“You don’t make a bad looking girl you know. Maybe the waist could be cinched in a little. And those heels bring out the best in your legs. Where is the hat?”

“I’m sorry mistress; I thought you would be requiring me to wear a wig again.”

“Not this time. But you do need make-up, so it’s a good thing you left the hat off for now.”

She sat me down and began to work at putting make-up on my face. After twenty minutes she stood back and handed me the hat. I looked into the mirror to help me put it on straight. Once more the face that looked back at me didn’t look like me, but again it gave my incarcerated dick a twitch.

“Come on nurse, there are patients waiting for us.” Sharon said. I took a last look at my reflection and then followed her out.

“Us, Mistress Sharon?”

“You don’t think you’re the only one who’s going to have some fun do you?”

We entered the main room and went to the main stage, around which were twenty or so naked men. Sharon stood with her hands on her hips.

“Come on then guys, form an orderly queue. The nurses will see you now.” She knelt in front of the first ‘patient’ and took his knob into her mouth. I followed suit, the guy’s cockhead rubbing against the roof of my mouth and into my throat. I was surprised at how easy it had become for me to take a cock in my throat. Part of me was still disgusted at my enjoyment of this new-found talent, but mainly I revelled in my cocksucking ability; I loved to give head now.